W hen designer fashion shop Raggs first opened in 1984, “people would pull over to buy a $200 sweater like they were buying milk,” quips owner Tom Maloney.

“Raggs” derives from a slang reference to the fashion industry—“the rag business.” (The extra “g”? Purely aesthetic.) Maloney and since-departed co-founder John LoRicco opened the boutique’s original location in Westville, at that time selling both men’s and women’s clothing. Now Raggs is a menswear-only fixture downtown, a member of Chapel Street’s retail row.

Despite occasional windfalls from incomprehensible phenomena like the luxury sweater craze of 1984, the fashion business is tough. Maloney points out that he has to stock “the right size, the right color, the right fit—you have to line everything up,” or else the customer’s walking away empty-handed. Then there’s the fact that fashion constantly changes, poised between what’s in and what’s next, but with hard inventory to sell in the meantime.

Happily for most men (so one guesses, anyway), our fashions change at a much slower clip than women’s. Consider men’s formalwear: with the exception of wild, relatively short-lived colored-tux experiments, the classic black tuxedo has reigned in America for over a century. Maybe a peak lapel is in style one decade and a notch lapel the next, but these are quibbles. Besides, your peaks will still get compliments.

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Now contrast the endurance of the black tuxedo with all the beautiful, expensive formal gowns worn just once to a gala or an opera, never to be seen in public again.

Raggs turns 29 this month, which, given how long the average small business lasts, is the equivalent of centuries in people-years. But Maloney doesn’t let that get in the way of the shop’s progressive aesthetic. It’s “all about a modern fit,” he says. The clothes at Raggs feature “a slimmer lay” and sit “closer to the body.” Maloney ticks off the benefits: “It’s more flattering, it’s less bulky, it’s streamlined.”

Such advantages require greater skill and refinement to design and produce in the first place, and come at a premium cost. Dress shirts typically ring up between $95 and $225; suit jackets between $395 and $595; and two-piece suits between $695 and $895. Sensibly, Raggs has partnerships with local tailors to do alterations and custom-fitting for those who want them, because, if you’re going to make an investment of several hundreds of dollars into what will soon be your best suit, it seems worth investing a little more to get the jacket’s sleeve length just right.

While it’s tempting to think of Raggs as a suit-and-tie shop, it’s something more than that, carrying a pretty thoughtful variety of items to round out its suits: dress shoes and boots with dress socks to slip on first; winter hats, dress gloves, scarves, sweaters and understated lightweight puffer coats to keep sartorially warm; designer denim for a more casual look, and formal touches like bow ties, cuff links, pocket squares; plus wide, slim wallets, and a small selection of watches, which includes a black Simon Carter model so handsome, so tasteful, that you might wonder if having it on your wrist isn’t worth being a little late on your rent next month.

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Undershirts and briefs behind the main counter seem at first to be out of place amidst all this finery. Then again, this is a man’s shop, and men know well the practical value of an undershirt in turning their thin white dress shirts from slightly sheer to resolutely opaque, and of having robust support down under.

It’s a subtle, or maybe not-so-subtle, sign that Maloney is a pragmatist in his own way, and there are other indications as well. He expresses appreciation for his wife, Lisa, who puts up with “being married to a small-business owner. You work pretty much six days a week,” and for his staff, such as George Fracasse, who, among other things, dresses all the store’s dapper, well-layered mannequins. He describes running Raggs as a “challenge that’s always there,” but says that it still carries a thrill, too, even after nearly 29 years.

“You get that certain customer who comes in your store, and they like what you have, and it’s amazing… There’s a guy out there who can appreciate this kind of clothing and can fit it, and that’s who we’re all about.”

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About Dan Mims

Turning down a dream editing job right out of college, Dan instead went into marketing and media sales to better cover the rent. Stints at Spin Magazine and Yahoo! followed. But he kept scratching that writing-and-editing itch—first on the side, then at a couple of startups. Dan is now scratching it as Daily Nutmeg's editor.